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Preparatino method of (2S,4S)-1-(4-nitro carbobenzoyl)-2-[(3-allyloxycarbonyl)-phenyl aminoformyl]-pyrrolidine -4-thioalcohol

A technology of phenylcarbamoyl and nitrobenzyloxycarbonyl, which is applied in the field of preparation of -1--2-[-phenylcarbamoyl]-pyrrolidin-4-yl mercaptan, and can solve the problem that it is not suitable for industrialization Difficulty in production, source of raw materials, and high toxic effects, to achieve the effect of cheap price, convenient source of raw materials, and reduction of three wastes

Inactive Publication Date: 2007-10-24
SHANGHAI JIAO TONG UNIV
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Problems solved by technology

[0009] In summary, the above-mentioned method in the prior art has the following deficiencies: 1, the first step adopts allyl bromide to carry out the esterification reaction, which is not only expensive, but also has a large toxic effect; 2, column chromatography is mostly used for product separation Purification is not suitable for industrial production; 3. In the third step reaction, (2S, 4S)-1-allyloxycarbonyl-2-hydroxycarbonylpyrrolidin-4-ylthiothioacetic acid ethyl ester is used as raw material, and the source of raw material Difficult, high production cost

Method used

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Embodiment Construction

[0028] Provide following embodiment in conjunction with content of the present invention:

[0029] (1) Preparation of N-p-nitrobenzyloxycarbonyl-4-hydroxyl-proline

[0030] Trans-4-hydroxyproline (20g, 153mmol) was dissolved in water (100ml), potassium carbonate (27.5g, 1.3equ.) was added under stirring, and PNZ-Cl (37.4g, 1.1equ.) was added dropwise in an ice-water bath .) in toluene (35 mL), kept stirring for 1 h, and monitored the end point of the reaction by TLC. Separate the water layer, decolorize it with activated carbon, add concentrated hydrochloric acid dropwise in an ice bath until the pH of the system is 2, stir continuously to avoid agglomeration, let stand for 2 hours, filter with suction, wash with appropriate amount of water, and dry to constant weight to obtain the product 45.8 g, y=96.4%.

[0031] 1H NMR (400MHz, DMSO-d 6 )δ: 8.23-8.16 (m, 2H, Ar-H), 7.62-7.56 (m, 2H, Ar-H), 5.26-5.11 (m, 2H, -OCH2-Ar), 4.33-4.17 (m, 2H , H-2 and H-4), 3.52-3.34(m, 2H, H-...

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Abstract

A process for preparing (2S, 4S)-1-(4-nitrobenzyloxycarbonyl)-2-[(3- allyloxycarbonyl)-phenylaminoformyl]-pyrrolidine-4-yl thiol includes such steps as reaction between trans-4-hydroxy-L-pyrrolidine and p-nitrobenzyl carbonyl chloride to obtain product A, the reaction of meta-nitrobenzoic acid on dichlorosulfoxide and then on allyl alcohol to obtain allyl meta-nitrobenzoate, reducing it by SnCl2 to obtain allyl meta-aminobenzoate, condensation reaction on said product A, activating the resultant by methylsulfuryl chloride, reaction on potassium thioacetate, and hydrolyzing.

Description

technical field [0001] The present invention relates to a synthesis method in the technical field of medicine, specifically a (2S,4S)-1-(4-nitrobenzyloxycarbonyl)-2-[(3-allyloxycarbonyl)-phenyl The preparation method of carbamoyl]-pyrrolidin-4-ylthiol. technical background [0002] (2S,4S)-1-(4-Nitrobenzyloxycarbonyl)-2-[(3-allyloxycarbonyl)-phenylcarbamoyl]-pyrrolidin-4-ylthiol is a novel antibiotic The key intermediate of ertapenem, ertapenem (ertapenem, MK-0826, L-749, 345, trade name INVANZTM) is a new type of broad-spectrum carbapenem antibiotic newly developed by Merck Pharmaceutical Company of the United States. This product was launched in the United States and Europe in November 2001 and April 2002 respectively. It is the only I-β-methyl carbapenem antibiotic for parenteral administration and has a wide range of antibacterial activities, including Gram-positive With negative aerobes and anaerobes. [0003] After searching the literature of the prior art, it was f...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/12
Inventor 张万斌刘德龙罗丽谢芳
Owner SHANGHAI JIAO TONG UNIV
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